(2S)-1-(tert-Butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid → Tert-butyl 2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate

HRID 350380Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@@:9]1([CH3:16])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C:9]1([CH2:10][OH:11])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of N-tert-butoxycarbonyl-2-methylproline (1.10 g, 4.80 mmol) in THF (20 mL) was added dropwise BH3-SMe2 (0.546 mL, 5.76 mmol) at room temp. After the resulting mixture was stirred for 6 hr at 80° C., the mixture was evaporated in vacuo. The residue was diluted with MeOH, washed with n-hexane (3×), and evaporated in vacuo to afford 0.648 g (60%) N-tert-butoxycarbonyl-2-hydroxymethyl-2-methylpyrrolidine as a yellow syrup. 1H-NMR (CDCl3) δ 1.47 (s, 9H), 1.76–2.05 (m, 4H), 3.28–3.48 (m, 2H), 3.66 (m, 2H, d).

Workup

customthe mixture was evaporated in vacuo
additionThe residue was diluted with MeOH
washwashed with n-hexane (3×)
customevaporated in vacuo

Sources & evidence

ORD record: ord-76db141a21d7411aa070f1c7714bc973
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179819B2

Reaction notes

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