Sodium borohydride → HCID 53700837, compound

HRID 1384313Notes

Reaction equation

HRID 1384313 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:21](=[O:37])[CH:22]([N:24]2[CH2:29][CH2:28][C:27]([OH:36])([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:26][CH2:25]2)[CH3:23])[CH:7]=[CH:8][C:9]=1[O:10][Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13]>C(O)C>[F:3][C:4]1[CH:5]=[C:6]([C@@H:21]([OH:37])[C@H:22]([N:24]2[CH2:25][CH2:26][C:27]([OH:36])([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:28][CH2:29]2)[CH3:23])[CH:7]=[CH:8][C:9]=1[O:10][Si:11]([CH:18]([CH3:19])[CH3:20])([CH:12]([CH3:13])[CH3:14])[CH:15]([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21186582HCID 21186582, compound

Product 1

HCID 53700837HCID 53700837, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of sodium borohydride (0.12 g, 3.17 mmol) and ethanol (5 mL) was stirred 10 min and then 1-(3-fluoro-4-triisopropylsilyloxyphenyl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-propan-1-one (1.41 g, 2.82 mmol in 25 mL of ethanol) was added. The reaction was stirred at ambient temperature overnight. The white precipitate which formed was collected by filtration to afford 0.14 g (10%) of (1R*,2R*)-1-(3-fluoro-4-triisopropylsilyloxyphenyl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-propan-1-ol which had: mp 140-141° C. Analysis calculated for C29H44FNO3Si: C, 69.42; H, 8.84; N, 2.79. Found: C, 69.30; H, 9.06; N, 2.84. The filtrate was quenched with water and stirred overnight. The resulting precipitate was collected, washed with water and air dried (1.5 g). This material was recrystallized from ethanol to afford 0.72 g of additional product for a total yield of 0.86 g (61%).

Workup

  1. stirringThe reaction was stirred at ambient temperature overnight
  2. customThe white precipitate which formed
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-dc0c2bfc47824d67ad0a2c0b097b6aba
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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