Water → (R)-tert-butyl 2-((S)-(3-chlorophenyl)(hydroxy)methyl)morpholine-4-carboxylate

HRID 253588Notes

Reaction equation

HRID 253588 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([C@@H:7]1[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)=[O:6].[BH4-].[Na+].O>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:5]([OH:6])[C@@H:7]2[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:8]2)[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 57786485(R)-tert-butyl 2-(3-chlorobenzoyl)morpholine-4-carboxylate

Product 1

HCID 57786497(R)-tert-butyl 2-((S)-(3-chlorophenyl)(hydroxy)methyl)morpholine-4-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-tert-butyl 2-(3-chlorobenzoyl)morpholine-4-carboxylate (5.5 g, 16.9 mmol) in MeOH (50 mL), NaBH4 (5.14 g, 135 mmol) was added in portions. The mixture was stirred overnight and water (50 mL) was added, The mixture was concentrated in vacuo until MeOH was removed. The aqueous residue was extracted with EtOAc. The organic extracts were washed with brine and dried over Na2SO4. The crude product was purified by chromatography to afford (R)-tert-butyl 2-((S)-(3-chlorophenyl)(hydroxy)methyl)morpholine-4-carboxylate (4.3 g, 78%)

Workup

  1. concentrationThe mixture was concentrated in vacuo until MeOH
  2. customwas removed
  3. extractionThe aqueous residue was extracted with EtOAc
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-b9f52ef1299d4cc48d946df0897e11f7
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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