tert-Butanol → Benzyl 3-(tert-butoxycarbonylamino)piperidine-1-carboxylate

HRID 458615ノート

反応式

HRID 458615 の反応式
[C:1]([N:11]1[CH2:19][CH2:18][CH2:17][C@@H:13](C(O)=O)[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[C:20]([OH:24])([CH3:23])([CH3:22])[CH3:21].C([N:27]([CH2:30]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:4]([O:3][C:1]([N:11]1[CH2:19][CH2:18][CH2:17][CH:13]([NH:27][C:30]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:39])[CH2:12]1)=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

参加物

7

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 7365381-(Phenylmethyl) (3R)-1,3-piperidinedicarboxylate

生成物 1

HCID 22258937Benzyl 3-(tert-butoxycarbonylamino)piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

(R)N-CBz nipecotic acid (86 g, 327 mmol) was dissolved in toluene (100 ml) and evaporated to dryness three times. tert. Butanol (1000 ml, 10.5 mmol) and triethylamine (50.1 ml, 359 mmol) were added to the reaction mixture. The reaction mixture was stirred for 30 min., and DPPA (98.5 ml, 457 mmol) was added over 15 min. The reaction mixture was heated to 100° C. overnight. After cooling, the solvent was removed by evaporation in vacuo, and water (200 ml) was added. After overnight stirring at RT the product was isolated by filtration, and stirred with EtOAc (250 ml) for one hour. The EtOAc solution was filtered and evaporated in vacuo to give the crude product as a white solid. This material was dissolved in hot EtOAc (200 ml), and cooled to 5° C. overnight. The precipitated product was isolated by filtration, washed with cold EtOAc and dried.

後処理

  1. customevaporated to dryness three times
  2. temperatureAfter cooling
  3. customthe solvent was removed by evaporation in vacuo, and water (200 ml)
  4. additionwas added
  5. stirringAfter overnight stirring at RT the product
  6. customwas isolated by filtration
  7. filtrationThe EtOAc solution was filtered
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-bc98a9a8e09044279ece8c1382e1812e
出典データセット
uspto-grants-2007_03
特許番号
US07192952B2

反応ノート

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