Sodium borohydride → HCID 54158084, compound

HRID 1384312Notes

Reaction equation

HRID 1384312 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]([C@@H:18]([OH:34])[C@H: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 54158084HCID 54158084, compoundYield 61.6%

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 min 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/ether/hexane and then 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/ether/hexane
  7. customrecrystallized from ethanol/ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-de7656789a1a47cd9b87442e51e49d6e
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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