Acetic Acid → HCID 24904639, compound

HRID 2167504Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClCCCl>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][N:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1

Participants

Conditions

Temperature: 45 °C

Procedure

To a mixture of pyrrolidin-3-ol (3.8 g, 44 mmol) and 3-methoxybenzaldehyde (5.0 g, 37 mmol) in 1,2-dichloroethane (100 mL), was added sodium triacetoxyborohydride (15.5 g, 73 mmol) portionwise at 0° C. Acetic acid (2.8 mL, 44 mmol) was subsequently added. The reaction mixture was warmed to 45° C. and stirred overnight. A saturated solution of sodium bicarbonate was added and the resulting mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product, 1-(3-methoxybenzyl)pyrrolidin-3-ol, obtained (6.0 g, 79%) as a yellow oil, was used as such in the next reaction: 1H NMR (CDCl3, 400 MHz) δ 7.28-7.18 (m, 1H), 6.92-6.86 (m, 2H), 6.82-6.76 (m, 1H), 4.32 (tdd, J=2.3, 5.0, 7.3 Hz, 1H), 3.83-3.78 (m, 3H), 3.59 (s, 2H), 2.86 (dt, J=4.9, 8.6 Hz, 1H), 2.68 (d, J=9.8 Hz, 1H), 2.53 (dd, J=5.3, 10.3 Hz, 1H), 2.45 (br s, 1H), 2.30 (dt, J=6.5, 8.9 Hz, 1H), 2.24-2.13 (m, 1H), 1.78-1.68 (m, 1H); ESI MS (m/z) 208 [M+H]+.

Workup

extractionthe resulting mixture was extracted with methylene chloride
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e4e75e6c9a1b419bb87e7bf91b0ea29e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045468B2

Reaction notes

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