Methanol → 2-Methyl-2-(pyrrolidin-1-yl)propan-1-ol
Reaction equation
[CH3:1][C:2]([N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:8])[C:3](OCC)=[O:4].[H-].[H-].[H-].[H-].[Li+].[Al+3].CO>C1COCC1.O>[CH3:1][C:2]([N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:8])[CH2:3][OH:4]Participants
6
Conditions
- Temperature
- 50 °C
Procedure
Ethyl 2-methyl-2-pyrrolidin-1-ylpropanoate (0.6162 g, 3.3308 mmol) was taken up in dry THF (5 mL). A 1M solution of LAH in THF (3.7 mL, 3.6639 mmol) was added drop wise. The reaction was warmed to 50° C. and stirred for 18 h. Cooleed to 0° C. in an ice bath and methanol (5 mL) was added slowly. The reaction was diluted with water (50 mL) and extracted with Et2O (2×50 mL). The organics were concentrated by blowing a slow stream of N2 over the flask to give 0.3578 g (2.0682 mmol, 62%) of the product as a light brown oil. 1H NMR (CDCl3) δ 3.22 (s, 2H), 2.61 (bs, 4H), 1.79 (bs, 4H), 1.01 (s, 6H).
Workup
- extractionextracted with Et2O (2×50 mL)
- concentrationThe organics were concentrated
Sources & evidence
- ORD record
- ord-86f14d7ad9984107a455816dad6194f9
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07285557B2
Reaction notes
Loading…