Methanol → HCID 59401903, compound

HRID 1516540Notes

Reaction equation

HRID 1516540 reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]([C@H:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)=O.CO>C1COCC1>[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C@H:9]1[CH2:13][CH2:12][NH:11][CH2:10]1

Participants

4

Reactant 2

HCID 887MethanolHCID 59401908HCID 59401908, compound

Product 1

HCID 59401903HCID 59401903, compoundYield 118.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2S,3S)-(2-Methyl-pyrrolidin-1-yl)-pyrrolidin-3-yl-methanone (2.3 mmol, as obtained above) in dry THF (6 mL) was added drop-wise 2 M solution of BH3SMe2 in THF (2M in THF, 5 mL, 10 mmol, 4 equiv.). The mixture was refluxed for 2 h. The solution was cooled to rt, 5 mL of methanol was added and stirred for 2 h at r.t. The solvent was evaporated to dryness to obtain 0.46 g of the title product as a semi-solid. LC/MS showed the molecular ion peak of the title compound at 169 (M+H) with a retention time of 1.742 min.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-2e492af437924f1d89250ea6aaa14bb8
Source dataset
uspto-grants-2012_07
Patent number
US08227504B2

Reaction notes

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