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

HRID 1400782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400782
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 232828431-Boc-4-(hydroxymethyl)-4-methylpiperidineAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-eb42f8501af44c58a0737111c0b807a1
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906929B2

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