Sodium borohydride → HCID 70654850, compound

HRID 2178202Notes

Reaction equation

HRID 2178202 reaction equation
[C:1]([CH2:3][S:4][C@H:5]1[CH2:9][O:8][CH2:7][C@@H:6]1[C@:10]([NH:19]C(=O)C(F)(F)F)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[CH3:11])#[N:2].[BH4-].[Na+]>C(O)C>[NH2:19][C@@:10]([C@H:6]1[CH2:7][O:8][CH2:9][C@@H:5]1[S:4][CH2:3][C:1]#[N:2])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[CH3:11]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86670225HCID 86670225, compound

Product 1

HCID 70654850HCID 70654850, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the crude N-[rel-(S)-1-((3S,4R)-4-cyanomethylsulfanyl-tetrahydro-furan-3-yl)-1-(2-fluoro-phenyl)-ethyl]-2,2,2-trifluoro-acetamide (2 g, 3.19 mmol) in ethanol (60 ml) was reacted with sodium borohydride (482 mg, 12.8 mmol) at 0° C. The reaction was left to warm to room temperature and stirred overnight. For the workup, the reaction mixture was extracted with a mixture of a saturated solution of sodium hydrogencarbonate and ethyl acetate. The combined organic layers were dried over sodium sulphate and evaporated at reduced pressure. The residue was purified by flash chromatography on silica gel using a gradient of heptane and ethyl acetate=100:0 to 0:100 as the eluent. The {rel-(3R,4S)-4-[(S)-1-amino-1-(2-fluoro-phenyl)-ethyl]-tetrahydro-furan-3-ylsulfanyl}-acetonitrile (510 mg, 57% yield) was obtained as a light yellow oil. MS (ISP): m/z=281.0 [M+H]+.

Workup

  1. waitThe reaction was left
  2. extractionFor the workup, the reaction mixture was extracted with a mixture of a saturated solution of sodium hydrogencarbonate and ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulphate
  4. customevaporated at reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel using a gradient of heptane and ethyl acetate=100:0 to 0:100 as the eluent

Sources & evidence

ORD record
ord-c6b08a5b3b824e4e8a6ca2b2d75c3e1e
Source dataset
uspto-grants-2015_06
Patent number
US09067924B2

Reaction notes

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