N-BOC-ethylenediamine → Tert-butyl 2-(2-tert-butoxybenzylamino)ethylcarbamate

HRID 403120ノート

反応式

HRID 403120 の反応式
[C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:12]([O:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=O)([CH3:15])([CH3:14])[CH3:13].[BH4-].[Na+]>CC#N>[C:12]([O:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][NH:11][CH2:10][CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:15])([CH3:13])[CH3:14]

参加物

5

反応物 3

HCID 187201N-BOC-ethylenediamineHCID 4311764Sodium borohydrideHCID 149555262-tert-Butoxybenzaldehyde

生成物 1

HCID 70896393Tert-butyl 2-(2-tert-butoxybenzylamino)ethylcarbamate収率 97%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

N-Boc-ethylenediamine (2.6 g, 16 mmol) and 8 (2.9 g, 16 mmol) were added to 250 mL of CH3CN and the reaction mixture was refluxed under argon for 4 hr. After cooling down to room temperature, the solvent was removed and the residue was redissolved in MeOH. The solvent was then evaporated and NaBH4 (3 g, 16 mmol) was added and stirred overnight. The solvent was evaporated, followed by extraction with CH2Cl2. The CH2Cl2 extract was concentrated and purified by a silica gel column using 2% methanolic NH3 (7 M NH3 in methanol/98% CH2Cl2 as eluent to yield the desired product as a pale yellow oil (97%). 1H NMR (CDCl3) δ 7.204 (dd, 1H, Ar), 7.115 (ddd, 1H, Ar), 7.007 (dd, 1H, Ar), 6.930 (ddd, 1H, Ar), 3.718 (s, 2H, —CH2—), 3.175 (d, 2H, —CH2—), 2.638 (t, 2H, —CH2—), 1.402 (s, 9H, —C(CH3)3), 1.382 (s, 9H, —C(CH3)3). Mass Spect.=323.23 (M+H)+.

後処理

  1. temperaturethe reaction mixture was refluxed under argon for 4 hr
  2. customthe solvent was removed
  3. dissolutionthe residue was redissolved in MeOH
  4. customThe solvent was then evaporated
  5. customThe solvent was evaporated
  6. extractionfollowed by extraction with CH2Cl2
  7. extractionThe CH2Cl2 extract
  8. concentrationwas concentrated
  9. custompurified by a silica gel column

出典と根拠

ORDレコード
ord-914755edcedb48aeac79fd04f99ca8c6
出典データセット
uspto-grants-2014_06
特許番号
US08747810B2

反応ノート

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