Sodium borohydride → HCID 70236294, compound

HRID 1384330Notes

Reaction equation

HRID 1384330 reaction equation
[BH4-].[Na+].[CH:3]([Si:6]([CH:36]([CH3:38])[CH3:37])([CH:33]([CH3:35])[CH3:34])[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:32])[CH:15]([N:17]2[CH2:22][CH2:21][C:20]([C:24]3[CH:29]=[C:28]([Br:30])[CH:27]=[C:26]([Br:31])[CH:25]=3)([OH:23])[CH2:19][CH2:18]2)[CH3:16])=[CH:10][CH:9]=1)([CH3:5])[CH3:4]>C(O)C>[CH:36]([Si:6]([CH:3]([CH3:5])[CH3:4])([CH:33]([CH3:35])[CH3:34])[O:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]([OH:32])[C@H:15]([N:17]2[CH2:18][CH2:19][C:20]([C:24]3[CH:29]=[C:28]([Br:30])[CH:27]=[C:26]([Br:31])[CH:25]=3)([OH:23])[CH2:21][CH2:22]2)[CH3:16])=[CH:10][CH:9]=1)([CH3:38])[CH3:37]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 21186609HCID 21186609, compound

Product 1

HCID 70236294HCID 70236294, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An ice cold mixture of sodium borohydride (0.21 g, 5.56 mmol) and ethanol (50 mL) was stirred 10 min and then 1-(4-triisopropylsilyloxyphenyl)-2-(4-(3,5-dibromophenyl)-4-hydroxypiperidin-1-yl)-propan-1-one (3.55 g, 5.56 mmol in 50 mL of ethanol) was added dropwise over 15 min. The reaction was allowed to warm to ambient temperature and stir overnight. Additional sodium borohydride (0.10 g) was added and the reaction was stirred 6 h more. The white precipitate was collected and rinsed with ethanol and weighed 0.84 g. The filtrate was treated with sodium borohydride (0.10 g) and stirred overnight. The white precipitate was collected and rinsed with ethanol and weighed 2.56 g. The combined precipitate (3.40 g) was recrystallized from ethanol to afford 3.0 g (84%) of (1R*,2R*)-1-(4-triisopropylsilyloxyphenyl)-2-(4-(3,5-dibromophenyl)-4-hydroxypiperidin-1-yl)-propan-1-ol as fluffy white needles which had: mp 235-236.5° C. Analysis calculated for C29H43Br2NO3Si: C, 54.29; H, 6.76; N, 2.18. Found: C, 54.17; H, 6.50; N, 2.35.

Workup

  1. stirringstir overnight
  2. stirringthe reaction was stirred 6 h more
  3. customThe white precipitate was collected
  4. washrinsed with ethanol
  5. additionThe filtrate was treated with sodium borohydride (0.10 g)
  6. stirringstirred overnight
  7. customThe white precipitate was collected
  8. washrinsed with ethanol
  9. customThe combined precipitate (3.40 g) was recrystallized from ethanol

Sources & evidence

ORD record
ord-6b9586ef47d449f38f1258529bee1d17
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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