Methanol → HCID 12073627, compound

HRID 561768Notes

Reaction equation

HRID 561768 reaction equation
S1[C:5]([C:6](=[O:34])/[CH:7]=[CH:8]/[C@H:9]2[C@@H:13]([F:14])[CH2:12][C@H:11]([O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[C@@H:10]2[CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29])=[CH:4][C:3]2[CH:35]=[CH:36][CH:37]=[CH:38][C:2]1=2.[BH4-].[Na+].[CH3:41]O>>[CH2:41]1[C:2]2[C:3](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:4][CH:5]1[C@H:6]([OH:34])/[CH:7]=[CH:8]/[C@H:9]1[C@@H:13]([F:14])[CH2:12][C@H:11]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[C@@H:10]1[CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29]

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 67000522HCID 67000522, compound

Product 1

HCID 12073627HCID 12073627, compound

Conditions

Temperature
-40 °C

Procedure

To a stirring mixture consisting of (Z)-isopropyl 7-((1R,2R,3S,5S)-2-((E)-3-(benzo[b]thiophen-2-yl)-3-oxoprop-1-enyl)-3-fluoro-5-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoate (prepared in Step H, 13.4 g) in methanol (325 mL) cooled to −40° C. was added CeCl3 heptahydrate (9.46 g). The reaction mixture was further cooled to −78° C. and was stirred for an additional hour. Sodium borohydride (1.89 g) was added and the reaction mixture was stirred for one hour at −78° C. Upon completion (as visualized by TLC), the reaction was quenched by the addition of acetone and the mixture was warmed to room temperature. The mixture was subsequently acidified with 5% KHSO4, extracted with DCM, and the organic layers were washed twice with brine. The organic phase was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude title intermediate (15.2 g). The crude intermediate was carried on with no further purification.

Workup

  1. temperatureThe reaction mixture was further cooled to −78° C.
  2. stirringthe reaction mixture was stirred for one hour at −78° C
  3. customUpon completion (as visualized by TLC), the reaction was quenched by the addition of acetone
  4. temperaturethe mixture was warmed to room temperature
  5. extractionextracted with DCM
  6. washthe organic layers were washed twice with brine
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f6d4c5b0d14b4b57bb0399e8cdf31ecb
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

Loading…