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

HRID 2071112노트

반응식

HRID 2071112 반응식
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

참가 물질

5

반응물 2

HCID 5003444Sodium cyanoborohydrideHCID 86647435(R)-benzyl 2-(4-(hydroxymethyl)oxazol-2-yl)pyrrolidine-1-carboxylate

생성물 1

HCID 86647436(R)-benzyl 2-(4-methyloxazol-2-yl)pyrrolidine-1-carboxylate수율 17.3%

시약·촉매·용매 2

HCID 2735090Methyltriphenoxyphosphonium iodide촉매HCID 12679Hexamethylphosphoramide용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d52c605f8578400da0032e7ef615ac0a
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

반응 노트

불러오는 중…