Tetrahydrofuran → Tert-butyl 6-triphenylmethyloxy-3(R),5(S)-dihydroxyhexanoate

HRID 1294047Notes

Reaction equation

HRID 1294047 reaction equation
[C:1]1([C:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:8][CH2:9][C@@H:10]([OH:22])[CH2:11][C:12](=[O:21])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.COB(CC)CC.[BH4-].[Na+]>O.C(O)(=O)C.CO>[C:29]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[O:8][CH2:9][C@@H:10]([OH:22])[CH2:11][C@@H:12]([OH:21])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 522516DiethylmethoxyboraneHCID 4311764Sodium borohydrideHCID 15702750t-Butyl (S)-5-hydroxy-3-oxo-6-(triphenylmethoxy)hexanoate

Product 1

HCID 57144739Tert-butyl 6-triphenylmethyloxy-3(R),5(S)-dihydroxyhexanoate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
-60 °C

Procedure

To the crude tert-butyl 6-triphenylmethyloxy-5(S)-hydroxy-3-oxohexanoate was added 150 mL of THF followed by 15 mL of MeOH and was chilled to −60° C. 26 mL of methoxydiethylborane (50% solution in THF) was added over a period of 20 minutes and stirring was continued for a further 30 minutes. The reaction mixture was cooled to −80° C. and 5 g of sodium borohydride was added in portions and the after completion of addition the reaction mixture was stirred for 5 hours at −78° C. Acetic acid was added to adjust the pH to 7 and water was added. The aqueous layer was extracted using EtOAC, washed with brine, dried and concentrated to give the title compound which was used as such for the next step.

Workup

  1. temperatureThe reaction mixture was cooled to −80° C.
  2. additionthe after completion of addition the reaction mixture
  3. stirringwas stirred for 5 hours at −78° C
  4. additionwas added
  5. extractionThe aqueous layer was extracted
  6. washwashed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d837fa3e0b3a4cbd9584ec037cfbf126
Source dataset
uspto-grants-2007_07
Patent number
US07238826B2

Reaction notes

Loading…