Dimethyl Sulfide → 1-Boc-4-(hydroxymethyl)-4-methylpiperidine

HRID 1400782노트

반응식

HRID 1400782 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH3:17])([C:14](O)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(C)C>C1COCC1>[OH:15][CH2:14][C:11]1([CH3:17])[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]1

참가 물질

4

반응물 2

HCID 1068Dimethyl SulfideHCID 232828481-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acid

생성물 1

HCID 232828431-Boc-4-(hydroxymethyl)-4-methylpiperidine수율 99.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A suspension of 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (0.750 g, 3.08 mmol) in THF (5 mL) at rt under N2 was treated with 2M THF solution of BH3 SMe2 (1.541 mL, 3.08 mmol). After 18 h, the reaction was cooled in an ice bath and quenched by the addition of 5 mL of 1N NaOH. Partitioned between ether and water. Organic phase dried (MgSO4), filtered, and concentrated in vacuo to give 700 mg (99%) of tert-butyl 4-(hydroxymethyl)-4-methylpiperidine-1-carboxylate as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 3.86-3.64 (m, 3H), 3.41 (s, 2H), 3.15 (ddd, J=13.6, 10.2, 3.5 Hz, 2H), 1.94-1.80 (m, 1H), 1.52-1.43 (m, 10H), 1.31 (dt, J=13.5, 3.8 Hz, 2H), 1.01 (s, 3H).

후처리

  1. temperaturethe reaction was cooled in an ice bath
  2. customquenched by the addition of 5 mL of 1N NaOH
  3. customPartitioned between ether and water
  4. dry with materialOrganic phase dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-eb42f8501af44c58a0737111c0b807a1
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906929B2

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