Sodium borohydride → N-Boc-(R)-2-(3-(hydroxymethyl)benzyl)morpholine

HRID 2253042Notes

Reaction equation

HRID 2253042 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=[O:22])[CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86607062(R)-2-(3-formyl-benzyl)-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 67073062N-Boc-(R)-2-(3-(hydroxymethyl)benzyl)morpholine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 0.48 g (1.6 mmol) (R)-2-(3-formyl-benzyl)-morpholine-4-carboxylic acid tert-butyl ester in 5 mL methanol was treated with 36 mg (0.95 mmol) sodium borohydride. After 2 h the reaction was diluted with ethyl acetate and extracted with 10% aqueous sodium bicarbonate solution and brine. The organic layer was dried over magnesium sulfate, filtered and evaporated. Chromatography of the remaining residue on silica gel with n-hexane:ethyl acetate (1:1 v/v) gave the desired compound in form of a colorless oil (87%).

Workup

  1. extractionextracted with 10% aqueous sodium bicarbonate solution and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-0c3f544dee274a5e81792869009f7ece
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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