Potassium Hydroxide → 1-[2-[4,5-Bis(4-methylphenyl)oxazol-2-yl]pyrrolidin-1-yl]-1,2,3,4-tetrahydro-5-t-butyldiphenylsilyloxynaphthalene

HRID 1741415

反応式

HRID 1741415 の反応式
[Si:1]([O:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][CH2:23][CH:24]2[NH2:29])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[N:38]=[C:39]([C:49](=O)[CH2:50][CH2:51][CH:52]=O)[O:40][C:41]=2[C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)=[CH:33][CH:32]=1.[BH3-]C#N.[Na+].[OH-].[K+]>C(O)(=O)C.CO>[CH3:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]2[N:38]=[C:39]([CH:49]3[CH2:50][CH2:51][CH2:52][N:29]3[CH:24]3[C:25]4[C:20](=[C:19]([O:18][Si:1]([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=5)[C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[CH:28]=[CH:27][CH:26]=4)[CH2:21][CH2:22][CH2:23]3)[O:40][C:41]=2[C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)=[CH:35][CH:36]=1

参加物

7

反応物 4

HCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 183672311,2,3,4-Tetrahydro-5-t-butyldiphenylsilyloxy-1-naphthaleneamineHCID 183673471-[4,5-Bis(4-methylphenyl)oxazol-2-yl)butan-1,4-dione

生成物 1

HCID 183672421-[2-[4,5-Bis(4-methylphenyl)oxazol-2-yl]pyrrolidin-1-yl]-1,2,3,4-tetrahydro-5-t-butyldiphenylsilyloxynaphthalene収率 94.8%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

A solution of 1,2,3,4-tetrahydro-5-t-butyldiphenylsilyloxy-1-naphthaleneamine (0.21 g), 1-[4,5-bis(4-methylphenyl)oxazol-2-yl)butan-1,4-dione (0.12 g), NaBH3CN (84 mg) and KOH (30 mg) in acetic acid (0.5 ml) and methanol (4 ml). After being stirred for 3 days at room temperature, the solvent was evaporated in vacuo. The residue was partitioned between ethyl acetate and sat. NaHCO3. The organic layer was washed with brine. The dried solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give 1-[2-[4,5-bis(4-methylphenyl)oxazol-2-yl]pyrrolidin-1-yl]-1,2,3,4-tetrahydro-5-t-butyldiphenylsilyloxynaphthalene (0.24 g). FABMS (m/z): 702 (M+ -1) NMR (CDCl3, δ): 1.08 (9H, s), 1.58-3.04 (12H, m), 2.34 (3H, s), 2.36 (3H, s), 6.18-7.80 (21H, m)

後処理

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate and sat. NaHCO3
  3. washThe organic layer was washed with brine
  4. customThe dried solvent was evaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-f18da2ce4fbe40ddb55e49c0bac305d2
出典データセット
uspto-grants-1999_10
特許番号
US05972965

関連ノート

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