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

HRID 2071112ノート

反応式

HRID 2071112 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 2735090Methyltriphenoxyphosphonium iodide触媒HCID 12679Hexamethylphosphoramide溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d52c605f8578400da0032e7ef615ac0a
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

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