Formaldehyde → HCID 23627568、化合物

HRID 1171903ノート

反応式

HRID 1171903 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 23627568HCID 23627568、化合物収率 91%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (Example 2) (73 mg, 0.2 mmol) in CH2Cl2 (5 mL) was treated with a 37% aqueous formaldehyde solution (16.4 uL, 0.22 mmol) and stirred for 5 min after which time solid sodium triacetoxyborohydride (64 mg, 0.3 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 product as a burgundy oil (69 mg, 91%). 1H NMR (CDCl3) 1.54-1.61 (m, 2H), 1.77-1.85 (m, 6H), 2.57 (s, 3H), 2.60-2.67 (m, 3H), 3.02-3.13 (m, 3H), 3.22-3.32 (m, 2H), 3.76 (s, 3H), 4.59-4.62 (m, 1H), 3.76 (s, 3 H), 4.59-4.62 (m, 1H), 6.30 (dd, J=8.6, 2.9, 1H), 6.35 (d, J=8.6, 1H), 7.20-7.33 (m, 5H). 13C NMR 24.2 (CH2), 33.0 (CH2), 36.3 (CH2), 42.9(CH3), 50.2 (CH2), 55.0 (CH2), 55.1 (CH2), 56.8 (CH3), 63.7 (CH), 80.4 (CH), 106.2 (CH), 107.8(CH), 113.2(CH), 126.4 (CH) 128.6, 129.5 (CH), 139.0 (CH), 144.5, 146.1, 148.4. LC/MS 5.10 min, [M+1]+ 381.

後処理

  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

出典と根拠

ORDレコード
ord-403e95c19c0a401ebe3bb4105e163d15
出典データセット
uspto-grants-2010_11
特許番号
US07829713B2

反応ノート

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