Sodium borohydride → HCID 57108154, compound

HRID 1384309Notes

Reaction equation

HRID 1384309 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:35])[C:16]([N:21]3[CH2:26][CH2:25][C:24]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)([OH:27])[CH2:23][CH2:22]3)=[CH:17][O:18]2)=[CH:13][C:12]=1[CH3:36])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([C@H:15]([OH:35])[C@H:16]([N:21]3[CH2:26][CH2:25][C:24]([C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)([OH:27])[CH2:23][CH2:22]3)[CH2:17][O:18]2)=[CH:13][C:12]=1[CH3:36])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 21186617HCID 21186617, compound

Product 1

HCID 57108154HCID 57108154, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of sodium borohydride (0.25 g, 6.61 mmol) and ethanol (5 mL) was stirred 10 min and then 7-benzyloxy-6-methyl-3-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-chromen-4-one (0.30 g, 0.653 mmol in 20 mL of ethanol and 15 mL of tetrahydrofuran) was added. The reaction was stirred at ambient temperature overnight. Additional sodium borohydride (0.12 g) was added and stirring was continued over the weekend. The reaction was quenched with water and concentrated. The residue was triturated with water and filtered to give a solid which was a 2:1 mixture of starting material and product. This material was stirred with hot ethanol and filtered. The solid which was collected weighed 0.2 g and was pure starting material which could be recycled in this reduction step. The ethanol filtrate was concentrated to afford 0.113 g of (3R*,4S*)-7-benzyloxy-6-methyl-3-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-chroman-4-ol which had: mp 201-202° C. This material was carried directly to the next step.

Workup

  1. stirringThe reaction was stirred at ambient temperature overnight
  2. stirringstirring
  3. customThe reaction was quenched with water
  4. concentrationconcentrated
  5. customThe residue was triturated with water
  6. filtrationfiltered
  7. customto give a solid which
  8. additiona 2:1 mixture of starting material and product
  9. filtrationfiltered
  10. customThe solid which was collected
  11. concentrationThe ethanol filtrate was concentrated

Sources & evidence

ORD record
ord-dd07238568264054a2ac3d8daea77b48
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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