Lithium borohydride → HCID 71020561, compound

HRID 455275Notes

Reaction equation

HRID 455275 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:9][C@H:8]([O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][N:6]1[C:28](=[O:42])[NH:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]([F:41])([F:40])[F:39])=[CH:32][CH:31]=1)=O.[Li+].[BH4-]>C1COCC1>[F:41][C:38]([F:39])([F:40])[CH2:37][O:36][C:33]1[CH:32]=[CH:31][C:30]([NH:29][C:28]([N:6]2[CH2:7][C@@H:8]([O:10][Si:11]([C:24]([CH3:27])([CH3:25])[CH3:26])([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:9][C@@H:5]2[CH2:3][OH:2])=[O:42])=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 70976291HCID 70976291, compound

Product 1

HCID 71020561HCID 71020561, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-1-[4-(2,2,2-trifluoro-ethoxy)-phenylcarbamoyl]-pyrrolidine-2-carboxylic acid methyl ester (5 g, 8.33 mmol) in THF (30 mL) was added LiBH4 (2M in THF, 6.25 mL) at 0° C. and stirred for 2 h. The mixture was quenched with AcOH at 0° C. and diluted with DCM. The organic layer was washed with sat NaHCO3 solution, dried over Na2SO4 and concentrated. The residue was purified through column chromatography over silica (elution with 40% ethyl acetate in hexane) to yield 4.3 g (91%) of the title compound as pale yellow sticky liquid. LC-MS: 573.6 [M+1]+.

Workup

  1. customThe mixture was quenched with AcOH at 0° C.
  2. additiondiluted with DCM
  3. washThe organic layer was washed with sat NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified through column chromatography over silica (elution with 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9394edfb002d4ad4950baf9976f20484
Source dataset
uspto-grants-2013_07
Patent number
US08497288B2

Reaction notes

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