Acetic Acid → HCID 178501211、化合物

HRID 1019900ノート

反応式

HRID 1019900 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[CH3:13][O:14][C:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([NH2:23])[CH2:19][CH2:18]1)=[O:16].C(O)(=O)C.C([BH3-])#N.[Na+]>ClCCCl.CO>[CH3:13][O:14][C:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([NH:23][CH2:11][C:9]2[CH:8]=[CH:7][C:6]3[O:1][CH2:2][CH2:3][O:4][C:5]=3[CH:10]=2)[CH2:19][CH2:18]1)=[O:16]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178501207HCID 178501207、化合物

生成物 1

HCID 178501211HCID 178501211、化合物収率 97.2%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 887Methanol溶媒

実験手順

2,3-Dihydro-benzo[1,4]dioxine-6-carbaldehyde (198 mg, 1.21 mmol, 1.0 eq) is added at room temperature to a stirred solution of trans-4-amino-cyclohexanecarboxylic acid methyl ester (200 mg, 1.21 mmol, 1.0 eq) in 1,2-dichloroethane (8 mL) and methanol (2 mL), followed by acetic acid (80 μL, 1.39 mmol, 1.15 eq) and sodium cyanoborohydride (99 mg, 1.57 mmol, 1.3 eq). After 15 hours stirring at room temperature, the reaction mixture is extracted with dichloromethane (3×20 mL) and a saturated sodium hydrogen carbonate aqueous solution (20 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford trans-4-[(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amino]-cyclohexanecarboxylic acid methyl ester as an orange oil (359 mg, 92% yield).

後処理

  1. extractionthe reaction mixture is extracted with dichloromethane (3×20 mL)
  2. dry with materialThe combined organic layers are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-2ad78e03d6f24a47b3a0b72ec8713f57
出典データセット
uspto-grants-2014_05
特許番号
US08716280B2

反応ノート

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