(Dimethyl sulfide)trihydroboron → (3S,5R)-3-Hydroxymethyl-5-methyl-nonanoic Acid Tert-butyl Ester

HRID 479054노트

반응식

HRID 479054 반응식
[C:1]([O:5][C:6](=[O:19])[CH2:7][C@H:8]([CH2:12][C@H:13]([CH3:18])[CH2:14][CH2:15][CH2:16][CH3:17])[C:9](O)=[O:10])([CH3:4])([CH3:3])[CH3:2].CSC.B>C1COCC1>[C:1]([O:5][C:6](=[O:19])[CH2:7][C@@H:8]([CH2:9][OH:10])[CH2:12][C@H:13]([CH3:18])[CH2:14][CH2:15][CH2:16][CH3:17])([CH3:2])([CH3:4])[CH3:3]

참가 물질

4

반응물 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 54500721HCID 54500721, 화합물

생성물 1

HCID 57065055(3S,5R)-3-Hydroxymethyl-5-methyl-nonanoic Acid Tert-butyl Ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of the crude acid 139 (6.14 mmol) in 30 mL THF at 0° C. was added borane-dimethyl sulfide complex (2.0 M soln in THF, 4.6 mL, 9.2 mmol), and the mixture was allowed to warm slowly to ambient temperature overnight. Additional BH3-DMS was added until the acid was completely consumed (ca. 5 mL). The reaction was quenched by addition of MeOH, then partitioned between Et2O and sat. NaHCO3 (aq). The phases were separated, and the organic phase washed with brine, dried (MgSO4), and concentrated to provide alcohol 140. LRMS: m/z 226.1; 1H NMR (CDCl3): δ3.63 (dd, J=11.0, 4.2 Hz, 1H), 3.42 (dd, J=11.0, 6.8 Hz, 1H), 2.30 (dd, J=14.9, 7.6 Hz, 1H), 2.20 (dd, J=14.9, 5.6 Hz, 1H), 2.03 (m, 2H), 1.42 (s, 9H), 1.24 (m, 6H), 1.02 (m, 2H), 0.85 (m, 6H). The crude product was used without purification.

후처리

  1. customwas completely consumed (ca. 5 mL)
  2. customThe reaction was quenched by addition of MeOH
  3. custompartitioned between Et2O and sat. NaHCO3 (aq)
  4. customThe phases were separated
  5. washthe organic phase washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-64edf9b27f6743dda16b2c7aab5a50aa
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642398B2

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