Sodium borohydride → HCID 76107969, compound

HRID 433124Notes

Reaction equation

HRID 433124 reaction equation
[BH4-].[Na+].[C:3]1([C:9]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:13][C:12]3[CH:14]=[CH:15][C:16]([C:18](=[O:34])[CH:19]([N:21]4[CH2:26][CH2:25][C:24]([OH:33])([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH2:23][CH2:22]4)[CH3:20])=[CH:17][C:11]=3[O:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)C>[C:35]1([C:9]2([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[O:13][C:12]3[CH:14]=[CH:15][C:16]([CH:18]([OH:34])[CH:19]([N:21]4[CH2:22][CH2:23][C:24]([OH:33])([C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=5)[CH2:25][CH2:26]4)[CH3:20])=[CH:17][C:11]=3[O:10]2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22225743HCID 22225743, compound

Product 1

HCID 76107969HCID 76107969, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of sodium borohydride (0.15 g, 3.97 mmol) and ethanol (5 mL) was stirred 10 minutes and then 1-(2,2-diphenyl-benzo(1,3)dioxol-5-yl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-propan-1-one (1.70 g, 3.36 mmol in 20 mL of ethanol) was added. The reaction was stirred at ambient temperature over the weekend. The white precipitate was collected, rinsed with ethanol and ether and air dried to afford 1.35 g of crude product. The product was recrystallized from ethanol/ethyl acetate/methylene chloride to give 1.05 g (61%) of 1R*, 2R*)-1-(2,2-diphenyl-benzo(1,3)dioxol-5-yl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-propan-1-ol which had: mp 224-224.5° C. Analysis calculated for C33H33NO4: C, 78.08; H, 6.55; N, 2.76. Found: C, 78.16; H, 6.46; N, 2.72.

Workup

  1. stirringThe reaction was stirred at ambient temperature over the weekend
  2. customThe white precipitate was collected
  3. washrinsed with ethanol and ether and air
  4. customdried
  5. customto afford 1.35 g of crude product
  6. customThe product was recrystallized from ethanol/ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-d0026657bbf54e0394befa807015dfc7
Source dataset
uspto-grants-2003_12
Patent number
US06667317B2

Reaction notes

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