4-(4-Fluorophenyl)piperidine → 1-Allyl-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine

HRID 279215ノート

反応式

HRID 279215 の反応式
[CH2:1]([N:4]1[CH2:8][CH:7]([CH:9]2[CH2:11][CH2:10]2)[CH:6]([CH:12]=O)[CH2:5]1)[CH:2]=[CH2:3].[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:1]([N:4]1[CH2:8][CH:7]([CH:9]2[CH2:11][CH2:10]2)[CH:6]([CH2:12][N:24]2[CH2:25][CH2:26][CH:21]([C:18]3[CH:17]=[CH:16][C:15]([F:14])=[CH:20][CH:19]=3)[CH2:22][CH2:23]2)[CH2:5]1)[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 27591364-(4-Fluorophenyl)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 226244751-allyl-3-(RS)-formyl-4-(SR)-(cyclopropyl)pyrrolidine

生成物 1

HCID 226244721-Allyl-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine収率 61.3%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

To a solution of 1.8 g (10 mmol) of 1-allyl-3-(RS)-formyl-4-(SR)-(cyclopropyl)pyrrolidine and 2.68 g (15 mmol) of 4-(4-fluorophenyl)piperidine in 30 mL of dichloroethane at rt was added portionwise 6.36 g (30 mmol) of sodiumtriacetoxyborohydride. After stirring for 3 h at rt, the reaction mixture was partitioned between CH2Cl2 and sat'd K2CO3. The organic fraction was dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chomatography (silica, ethyl acetate:hexanes, 1:3) to give 2.1 g of the title compound.

後処理

  1. customthe reaction mixture was partitioned between CH2Cl2
  2. dry with materialThe organic fraction was dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chomatography (silica, ethyl acetate:hexanes, 1:3)

出典と根拠

ORDレコード
ord-f2f93066fb644903859a466072cb27f8
出典データセット
uspto-grants-2002_03
特許番号
US06362201B1

反応ノート

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