Diisopropylethylamine → (S)-tert-butyl 2-((1R,2R)-2-(4-bromophenyl)-1-(methoxycarbonyl)cyclopropylcarbamoyl)piperidine-1-carboxylate

HRID 600311ノート

反応式

HRID 600311 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:51][C@:52]1([C:62]([O:64][CH3:65])=[O:63])[CH2:54][C@@H:53]1[C:55]1[CH:60]=[CH:59][C:58]([Br:61])=[CH:57][CH:56]=1>CN(C=O)C>[Br:61][C:58]1[CH:57]=[CH:56][C:55]([C@H:53]2[CH2:54][C@:52]2([NH:51][C:14]([C@@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13][N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:16])[C:62]([O:64][CH3:65])=[O:63])=[CH:60][CH:59]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 688617(2S)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67268087(1R,2R)-methyl 1-amino-2-(4-bromophenyl)cyclopropanecarboxylate hydrochloride

生成物 1

HCID 57999639(S)-tert-butyl 2-((1R,2R)-2-(4-bromophenyl)-1-(methoxycarbonyl)cyclopropylcarbamoyl)piperidine-1-carboxylate収率 34.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (S)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (9.05 mg) in DMF (3 mL) was added Hunig's Base (0.019 mL) followed by HATU (15 mg). The mixture was allowed to stir at room temp for 10 min. To this solution was added in one portion (1R,2R)-methyl 1-amino-2-(4-bromophenyl)cyclopropanecarboxylate hydrochloride (11 mg) and the mixture was stirred overnight. The mixture was evaporated to dryness, the residue extracted into diethyl ether and washed well with water and brine, then dried over sodium sulfate. The sample was passed through a small silica plug/eluting with diethyl ether to give (S)-tert-butyl 2-((1R,2R)-2-(4-bromophenyl)-1-(methoxycarbonyl)cyclopropylcarbamoyl)piperidine-1-carboxylate (6 mg) as a colourless oil.

後処理

  1. stirringthe mixture was stirred overnight
  2. customThe mixture was evaporated to dryness
  3. extractionthe residue extracted into diethyl ether
  4. washwashed well with water and brine
  5. dry with materialdried over sodium sulfate

出典と根拠

ORDレコード
ord-9164d3eae90649d6ad0938a7b9a3db49
出典データセット
uspto-grants-2011_03
特許番号
US07902181B2

反応ノート

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