Sodium Hydroxide → Tert-butyl[3-(7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]carbamate

HRID 2078442ノート

反応式

HRID 2078442 の反応式
Cl.Cl.[CH2:3]([N:10]1[CH2:17][CH:16]2[O:18][CH:12]([CH2:13][NH:14][CH2:15]2)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].CC1C=C(C)C=C(C)C=1S(O[CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])(=O)=O>C1(C)C=CC=CC=1>[C:41]([O:40][C:38](=[O:39])[NH:37][CH2:36][CH2:35][CH2:34][N:14]1[CH2:15][CH:16]2[O:18][CH:12]([CH2:11][N:10]([CH2:3][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:17]2)[CH2:13]1)([CH3:44])([CH3:43])[CH3:42]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 185403703-(Phenylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane, hydrochloride (1:2)HCID 866280503-(tert-Butyloxycarbonylamino)propyl 2,4,6-trimethylbenzenesulfonate

生成物 1

HCID 15980224Tert-butyl[3-(7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]carbamate収率 90.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
65 °C

実験手順

To 3-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane dihydrochloride (25.08 g, 86.12 mmol; see Preparation O above) was added 2.5 M sodium hydroxide (115 mL). 3-(tert-Butyloxycarbonylamino)propyl 2,4,6-trimethylbenzenesulfonate (32.35 g, 90.50 mmol; see Preparation L above) and toluene (65 mL) were then added and the reaction mixture heated at 65° C. for 12 hours. The phases were separated at 65° C. and the lower (aqueous) layer discarded. The organic phase was re-heated to 65° C. and then extracted with 10% w/w aqueous citric acid (125 mL). The phases were separated and the upper (organic) phase discarded. To the aqueous citric acid phase was added isopropyl acetate (150 mL) and 5 M sodium hydroxide (75 mL). The resulting mixture was stirred at room temperature for 15 minutes. The phases were separated and the lower (aqueous) phase discarded. The resulting organic phase was dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound as a colourless oil (29.13 g, 77.60 mmol, 90%).

後処理

  1. customThe phases were separated at 65° C.
  2. temperatureThe organic phase was re-heated to 65° C.
  3. extractionextracted with 10% w/w aqueous citric acid (125 mL)
  4. customThe phases were separated
  5. additionTo the aqueous citric acid phase was added isopropyl acetate (150 mL) and 5 M sodium hydroxide (75 mL)
  6. customThe phases were separated
  7. dry with materialThe resulting organic phase was dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-25ad5fa932a4471a9815abb80ea50374
出典データセット
uspto-grants-2011_04
特許番号
US07928225B2

反応ノート

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