Reaction equation
C1(C)C=CC(S(N2C[C@H](O)C[C@H]2CO)(=O)=O)=CC=1.C[O:20][C:21](=O)[C@:22]1([OH:37])[CH2:26][CH2:25][CH2:24][N:23]1[S:27]([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28].[Li+].[BH4-].Cl>C1COCC1>[S:27]([N:23]1[CH2:24][CH2:25][CH2:26][C@@:22]1([OH:37])[CH2:21][OH:20])([C:30]1[CH:31]=[CH:32][C:33]([CH3:34])=[CH:35][CH:36]=1)(=[O:28])=[O:29]Participants
Conditions
- Temperature
- 0 °C
Procedure
(2S,4R)-1-(4-toluenesulfonyl)-2-hydroxymethyl-4-hydroxy pyrrolidine. To a solution of N-tosylhydroxy-L-proline methyl ester (62.20 g, 0.21 mole) in THF (600 mL) at 0° C. was added LiBH4 (15.8 g, 0.73 mole) in small portions. The reaction mixture was stirred at 0° C. for 1 h and allowed to stand at 23° C. for 18 h. The reaction mixture was cooled to -20° C., made neutral with 6N HCl and concentrated under reduced pressure. The residue was treated with water (550 ml) and extracted with EtOAc (4×300 mL). The combined organic extracts were washed with H2O, dried over MgSO4, filtered and concentrated under reduced pressure to give N-tosylhydroxy-L-prolinol as a white solid (50.56 g, 88.8%) which was used in the next step without further purification.
Workup
- waitto stand at 23° C. for 18 h
- temperatureThe reaction mixture was cooled to -20° C.
- concentrationconcentrated under reduced pressure
- additionThe residue was treated with water (550 ml)
- extractionextracted with EtOAc (4×300 mL)
- washThe combined organic extracts were washed with H2O
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-a7d70a7f216e4b2a979841fd9943d525
- Source dataset
- uspto-grants-1991_02
- Patent number
- US04994460
Linked notes
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