Sodium cyanoborohydride → (R)-benzyl 2-(4-methyloxazol-2-yl)pyrrolidine-1-carboxylate

HRID 2071112Notes

Reaction equation

O[CH2:2][C:3]1[N:4]=[C:5]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[O:6][CH:7]=1.[BH3-]C#N.[Na+]>CN(P(N(C)C)(N(C)C)=O)C.[I-].C[P+](OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>[CH3:2][C:3]1[N:4]=[C:5]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[O:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (R)-benzyl 2-(4-(hydroxymethyl)oxazol-2-yl)pyrrolidine-1-carboxylate (1.1 g, 3.64 mmoles) in HMPA (18 mL), was added methyltriphenoxyphosphonium iodide (3.29 g, 7.28 mmoles) and stirred for 30 min. Then NaCNBH3 was added and the reaction was heated at 50° C. for 3 h and poured into 100 mL of ice-cold water and extracted with ether (2×100 mL). The organic layer was dried on Na2SO4, concentrated, and chromatographed on silica gel (50% ethyl acetate/50% hexanes) to yield 180 mg of (R)-benzyl 2-(4-methyloxazol-2-yl)pyrrolidine-1-carboxylate.

Workup

extractionextracted with ether (2×100 mL)
customThe organic layer was dried on Na2SO4
concentrationconcentrated
customchromatographed on silica gel (50% ethyl acetate/50% hexanes)

Sources & evidence

ORD record: ord-d52c605f8578400da0032e7ef615ac0a
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299267B2

Reaction notes

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