Cyclopentyl methyl ether → HCID 58468017, compound

HRID 1879376Notes

Reaction equation

HRID 1879376 reaction equation
[BH4-].[Li+].COC1CCCC1.[F:10][C:11]1[CH:12]=[C:13]([C@@H:18]2[CH2:28][CH2:27][C@@H:26]([O:29][Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[C:19]2=[O:40])[CH:14]=[C:15]([F:17])[CH:16]=1>>[F:10][C:11]1[CH:12]=[C:13]([C@@H:18]2[CH2:28][CH2:27][C@@H:26]([O:29][Si:30]([CH:34]([CH3:36])[CH3:35])([CH:37]([CH3:39])[CH3:38])[CH:31]([CH3:32])[CH3:33])[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[C@H:19]2[OH:40])[CH:14]=[C:15]([F:17])[CH:16]=1

Participants

4

Reactant 3

HCID 138539Cyclopentyl methyl etherHCID 4148881Lithium borohydrideHCID 67115853HCID 67115853, compound

Product 1

HCID 58468017HCID 58468017, compoundYield 56%

Conditions

Temperature
0 °C

Procedure

Lithium borohydride (0.283 g, 13.01 mmol) was added to a cyclopentyl methyl ether (15 mL) solution of (6S,9R)-6-(3,5-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one (1.4496 g, 3.25 mmol) at 0° C. under nitrogen. The reaction was stirred at 0° C. for 6 h at room temperature. The reaction was quenched by adding methanol and continued to stir for 0.5 h. The solvent was removed via vacuum and the crude residue was taken up in ethyl acetate, which was washed by water three times. Flash chromatography using ethyl acetate in hexane from 0 to 10% gave the desired product (56%). HPLC tR=3.05 min,

Workup

  1. customThe reaction was quenched
  2. additionby adding methanol
  3. stirringto stir for 0.5 h
  4. customThe solvent was removed via vacuum
  5. washwhich was washed by water three times

Sources & evidence

ORD record
ord-d031a02e88fd4ac6bb81193ddee8036d
Source dataset
uspto-grants-2012_11
Patent number
US08314117B2

Reaction notes

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