Sodium borohydride → HCID 59598494, compound

HRID 2266286Notes

Reaction equation

HRID 2266286 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][C@@H:7]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[CH:29]=1)[C@@H:8]1[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1)C.[BH4-].[Na+]>CO>[F:27][C:23]1[C:22]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[CH:29]=2)=[C:21]([C@H:7]([O:6][CH2:5][CH2:4][OH:3])[C@@H:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:9]2)[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59598506HCID 59598506, compound

Product 1

HCID 59598494HCID 59598494, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-tert-butyl 2-((S)-(2-ethoxy-2-oxoethoxy)(6-fluoro-3′-methylbiphenyl-2-yl)methyl)morpholine-4-carboxylate (570 mg, 1.17 mmol) in CH3OH (20 mL) at rt, NaBH4 (355 mg, 9.36 mmol) was added in portions. The mixture was stirred for ˜0.5 h at rt and then evaporated. The residue was partitioned between water and EtOAc. The combined organic layers were washed with brine, dried over anhydrous NaSO4 and evaporated to give semi-crude (R)-tert-butyl 2-((S)-(6-fluoro-3′-methylbiphenyl-2-yl)(2-hydroxyethoxy)methyl)morpholine-4-carboxylate (498 mg, 96%), which was used in the next step reaction without further purification. MS (E/Z): 446 (M+H+)

Workup

  1. customevaporated
  2. customThe residue was partitioned between water and EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous NaSO4
  5. customevaporated

Sources & evidence

ORD record
ord-cc942ba5649d4f9d8af8190416cb39be
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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