Chloroform → Phenylmethyl 2-hydroxy-3,3-dimethyl-1-pyrrolidinecarboxylate

HRID 1014153Notes

Reaction equation

[CH3:1][C:2]1([CH3:18])[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C:3]1=[O:17].[BH4-].[Na+].C(Cl)(Cl)Cl.[NH4+].[Cl-]>CO.CCOC(C)=O>[OH:17][CH:3]1[C:2]([CH3:18])([CH3:1])[CH2:6][CH2:5][N:4]1[C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8]

Participants

Conditions

Temperature: -10 °C

Procedure

In a 500 ml flask was dissolved phenylmethyl 3,3-dimethyl-2-oxo-1-pyrrolidinecarboxylate (0.0494 mol, 12.2 g) in 100 ml methanol. The mixture was cooled to −10° C. and sodium borohydride (0.247 mol, 9.35 g) was added slowly in portions with stirring, maintaining an internal temperature below −5° C. After the addition TLC (90:10 CHCl3:EtOAc) confirmed reaction was complete. The mixture was poured onto 500 ml saturated aqueous NH4Cl with crushed ice and stirred 16 hours, after which time the aqueous phase was extracted with Et2O (2×200 ml). The organics were dried over MgSO4, filtered and concentrated yielding 11.8 g (96%) of phenylmethyl 2-hydroxy-3,3-dimethyl-1-pyrrolidinecarboxylate as a clear oil which was used without further purification. LCMS (ESI+)=232 m/z ([M-OH]+). 1H NMR (400 MHz, CDCl3)— rotamers δ 7.39-7.33 (m, 5H), 5.25-5.14 (m, 2H), 4.99 and 4.92 (s, 1H), 3.61-3.38 (m, 2H), 1.97-1.91 (m, 1H), 1.62-1.56 (m, 1H), 1.12 (s, 3H), 1.02 (s, 3H).

Workup

temperaturemaintaining an internal temperature below −5° C
customreaction
stirringstirred 16 hours
extractionafter which time the aqueous phase was extracted with Et2O (2×200 ml)
dry with materialThe organics were dried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-0f0da64585a445ff9f92a1047b19c5b4
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07982053B2

Reaction notes

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