Sodium Bicarbonate → HCID 67073052, compound

HRID 2253030Notes

Reaction equation

HRID 2253030 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([C:14](=[O:31])[C:15]2[CH:20]=[C:19]([F:21])[C:18]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:17][C:16]=2[F:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C(=O)(O)[O-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH:14]([C:15]2[CH:20]=[C:19]([F:21])[C:18]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:17][C:16]=2[F:30])[OH:31])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 67073314HCID 67073314, compound

Product 1

HCID 67073052HCID 67073052, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7.5 g of (S)-2-(4-benzyloxy-2,5-difluoro-benzoyl)-morpholine-4-carboxylic acid tert-butyl ester in methanol (90 ml) was added with cooling (0-5° C.) sodium borohydride (660 mg) in small portions. Stirring continued for 15 minutes with cooling before sodium bicarbonate (150 mL, saturated) was added. Organic material was partitioned into ethyl acetate (3×), organic phases were pooled, washed with brine and dried with Na2SO4 before being concentrated in vacuo to give 7.5 g of the title compound.

Workup

  1. additionwas added
  2. customOrganic material was partitioned into ethyl acetate (3×), organic phases
  3. washwashed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationbefore being concentrated in vacuo

Sources & evidence

ORD record
ord-19b469b794bc454ca2479301d003fcf3
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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