Nitrogen → HCID 131717470, compound

HRID 654628Notes

Reaction equation

HRID 654628 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([O:30][CH3:31])=[C:6]([C@H:12]2[CH2:16][CH2:15][C@H:14]([C:17]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=3)[C:13]2=[O:29])[S:7][C:8]=1[CH2:9][CH2:10][CH3:11])[CH3:2].[BH4-].[Na+].N#N>CO>[CH2:1]([O:3][C:4]1[C:5]([O:30][CH3:31])=[C:6]([CH:12]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:18]=[C:19]([O:27][CH3:28])[C:20]([O:25][CH3:26])=[C:21]([O:23][CH3:24])[CH:22]=3)[CH:13]2[OH:29])[S:7][C:8]=1[CH2:9][CH2:10][CH3:11])[CH3:2]

Participants

5

Reactant 3

HCID 947NitrogenHCID 4311764Sodium borohydrideHCID 67914249HCID 67914249, compound

Product 1

HCID 131717470HCID 131717470, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of crude trans-2-(4-ethoxy-3-methoxy-5-n-propylthiophenyl)-5-(3,4,5-trimethoxyphenyl)cyclopentanone (6.87 g, 14.5 mmoles) in MeOH (230 ml) was added at room temperature NaBH4 (1.64 g, 43.4 mmoles) in several portions over 5 minutes. The solution was stirred at room temperature in a N2 atmosphere for 21 hours and most of the MeOH removed in vacuo. The residue was suspended in H2O and extracted with Et2O (4×). The combined extracts were washed with H2O (3×) and saturated NaCl solution and dried (MgSO4). The residue after evaporation of the Et2O in vacuo was filtered through a 9.5×11 cm column of silica gel (E. Merck, Kriselgel 60 ) with (1:1) EtOAc-hexane (21). Evaporation in vacuo gave 6.12 g of a crude mixture of cyclopentanols. Separation by HPLC on a Prep 500 with silica gel and 2:1 hexane-EtOAc gave 2.27 g (33 % from 1) of 1β, 2β, 5α)-2-(4-ethoxy-3-methoxy-5-n-propylthiophenyl)-5-(3,4,5-trimethoxyphenyl)cyclopentanol (5, eluted first).

Workup

  1. customremoved in vacuo
  2. extractionextracted with Et2O (4×)
  3. washThe combined extracts were washed with H2O (3×) and saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. customThe residue after evaporation of the Et2O in vacuo
  6. filtrationwas filtered through a 9.5×11 cm column of silica gel (E. Merck, Kriselgel 60 ) with (1:1) EtOAc-hexane (21)
  7. customEvaporation in vacuo
  8. customgave 6.12 g of a crude mixture of cyclopentanols
  9. customSeparation by HPLC on a Prep 500 with silica gel and 2:1 hexane-EtOAc

Sources & evidence

ORD record
ord-7254bd2c7cb8425f8641280eae66fe73
Source dataset
uspto-grants-1992_07
Patent number
US05132463

Reaction notes

Loading…