2-Dimethylaminopyridine → 6-Benzyloxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic Acid (1S)-1-Methylheptyl Ester

HRID 48109

反応式

HRID 48109 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][CH:14]([C:19]([OH:21])=[O:20])[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][C@@H:23](O)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].CN(C1C=CC=CN=1)C>C1COCC1.C(N=C=NC(C)C)(C)C>[CH3:22][C@H:23]([O:20][C:19]([CH:14]1[CH2:13][CH2:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:10]=2)[CH2:15]1)=[O:21])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

参加物

6

反応物 3

HCID 218852-DimethylaminopyridineHCID 80080(R)-2-OctanolHCID 190699736-Benzyloxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic Acid

生成物 1

HCID 600724546-Benzyloxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic Acid (1S)-1-Methylheptyl Ester収率 53%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 12734Diisopropylcarbodiimide溶媒

実験手順

To a solution of 6-benzyloxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (31) (1 equi.), (R)-1-methylheptyl-1-ol (13) (1 equi.), and DMAP (dimethylaminopyridine) (0.1 equi.) in THF (25 mL/mmole), DIC (diisopropyl carbodiimide) (1.2 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane(1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (3% EtOAc/hexanes) gave 6-benzyloxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (1S)-1-methylheptyl ester (36) as a colorless oil (53%).

後処理

  1. customquenched with water
  2. extractionextracted with ethyl acetate:hexane(1:1)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (3% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-c8ea22bf38ec485ea92d25a7430e1238
出典データセット
uspto-grants-2004_03
特許番号
US06703082B1

関連ノート

読み込み中…