Claims
- 1. In a process for producing (RS,RS) morpholine diasteroisomers of formula (A) ##STR10## wherein R is C.sub.1 -C.sub.6 alkoxy or tri-halomethyl;
- wherein a (RS,RS) 3-substituted derivative of 1-amino-2-hydroxy-propane of formula (I) ##STR11## wherein R is as defined above, is converted to said (RS,RS) morpholine diastereoisomers of formula (A), the improvement comprising converting a (RS,RS) diastereoisomer of formula (I) to a (RS,RS) morpholine diastereoisomer of formula (A), wherein a (RS,RS) diastereoisomer of formula (I) is produced by the steps of:
- (a) epoxidizing trans-cinnamic alcohol to obtain the (RS,RS) compound of formula (II) ##STR12## (b) reacting the (RS,RS) compound of formula (II) with a phenol derivative of formula (III) ##STR13## wherein R is as defined above, to obtain a (RS,SR) 3-substituted-1,2-dihydroxy propane derivative of formula (IV) ##STR14## wherein R is as defined above; and (c) esterifying a (RS,SR) compound of formula (IV) with a carboxylic acid, or a reactive derivative thereof, to obtain a (RS,SR) compound of formula (VI) ##STR15## wherein R.sub.2 is the residue of a carboxylic acid and R is as defined above;
- (d) esterifying a (RS,SR) compound of formula (VI) with a sulfonic acid, or a reactive derivative thereof, to obtain a (RS,SR) diester of formula (VII) ##STR16## wherein R, R.sub.1 and R.sub.2 are as defined above; (e) making an epoxide from a (RS,SR) compound of formula (VII), to obtain a (RS,RS) compound of formula (VIII) ##STR17## wherein R is as defined above, and then reacting a (RS,RS) compound of formula (VIII) with ammonia, to obtain a (RS,RS) diastereoisomer of formula (I).
- 2. The process according to claim 1 for preparing a (RS,RS) 2[.alpha.-(2-ethoxy-phenoxy)-benzyl]morpholine compound of formula (A) wherein R is ethoxy.
Priority Claims (1)
Number |
Date |
Country |
Kind |
8419683 |
Aug 1984 |
GBX |
|
Parent Case Info
This is a division of application Ser. No. 08/027,585, filed Mar. 5, 1993, which is a continuation of Ser. No. 07/921,381, filed Jul. 30, 1992, which is a continuation of Ser. No. 07/560,499, filed Jul. 25, 1990, which is a continuation of Ser. No. 07/410,036, filed Sep. 21, 1989, which is a continuation of Ser. No. 07/139,592, filed Dec. 30, 1987, which is a divisional of Ser. No. 07/016,505, filed Jan. 27, 1987, which is a continuation of Ser. No. 06/751,858, filed Jul. 5, 1985, all abandoned.
US Referenced Citations (10)
Non-Patent Literature Citations (1)
Entry |
Banzatti et al., "Synthesis of Phenyl-substituted 2H-3,4-Dihydro-3-aminomethyl-1,4-benzoxazines", J. Heterocyclic Chem 20, 259-265(1983). |
Divisions (2)
|
Number |
Date |
Country |
Parent |
27585 |
Mar 1993 |
|
Parent |
16505 |
Jan 1987 |
|
Continuations (5)
|
Number |
Date |
Country |
Parent |
921381 |
Jul 1992 |
|
Parent |
560499 |
Jul 1990 |
|
Parent |
410036 |
Sep 1989 |
|
Parent |
139592 |
Dec 1987 |
|
Parent |
751858 |
Jul 1985 |
|