Acetic Acid → HCID 178501211, 화합물

HRID 1422735노트

반응식

HRID 1422735 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 178501211HCID 178501211, 화합물수율 97.2%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5a0985de325b40cf9f4b38a77fd8ba04
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927542B2

반응 노트

불러오는 중…