Formaldehyde → HCID 23627568, 화합물

HRID 1423113노트

반응식

HRID 1423113 반응식
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:30](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[CH3:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 16725642(S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine

생성물 1

HCID 23627568HCID 23627568, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (73 mg, 0.20 mmol) in CH2Cl2 (5 mL) was treated with a 37% aqueous formaldehyde solution (16 μL, 0.22 mmol) and stirred for 5 min after which time solid sodium triacetoxyborohydride (64 mg, 0.30 mmol) was added. The suspension was then stirred for 3 hr then quenched with a saturated aqueous NaHCO3 solution (2 mL). The organic component was separated, dried over MgSO4, filtered, and evaporated to an oil which was purified by silica gel flash chromatography with 5% MeOH/CH2Cl2 as eluant to afford the title compound as a burgundy oil (69 mg, 91%). 1H NMR (CDCl3) 7.33-7.20 (m, 5H), 6.72 (d, J=8.6, 1H), 6.35 (d, J=2.9, 1H), 6.30 (dd, J=8.6, 2.9, 1H), 4.62-4.59 (m, 1H), 3.76 (s, 3H), 3.32-3.22 (m, 2H), 3.13-3.02 (m, 3H), 2.67-2.60 (m, 4H), 2.57 (s, 3H), 1.85-1.77 (m, 6H), 1.61-1.54 (m, 2H). 13C NMR 148.4, 146.1, 144.5, 139.0 (CH), 129.5 (CH), 128.6, 126.4 (CH), 113.2 (CH), 107.8 (CH), 106.2 (CH), 80.4 (CH), 63.7 (CH), 56.8 (CH3), 55.1 (CH2), 55.0 (CH2), 50.2 (CH2), 42.9 (CH3), 36.3 (CH2), 33.0 (CH2), 24.2 (CH2). LC/MS (Method A) 5.10 min, [M+1]+ 381.

후처리

  1. additionwas added
  2. customthen quenched with a saturated aqueous NaHCO3 solution (2 mL)
  3. customThe organic component was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to an oil which
  7. customwas purified by silica gel flash chromatography with 5% MeOH/CH2Cl2 as eluant

출처 및 근거

ORD 기록
ord-400df85a0cf24a66810af24cd8b0040f
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927546B2

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