Hydrochloric Acid → Ammonia

HRID 1433256ノート

反応式

HRID 1433256 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][C:10]=1[C@@H:18]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:19][CH2:20][N:21]([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OC(C)(C)C)=O)=N\C(OC(C)(C)C)=O.C(OC(=O)[NH:75][CH2:76][CH2:77][C:78]1[CH:83]=[CH:82][C:81](O)=[CH:80][CH:79]=1)(C)(C)C.Cl>O1CCCC1>[NH3:21].[NH2:75][CH2:76][CH2:77][C:78]1[CH:83]=[CH:82][C:81]([O:17][CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:10]([C@@H:18]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:19][CH2:20][N:21]([CH:25]([CH3:26])[CH3:27])[CH:22]([CH3:23])[CH3:24])[CH:11]=2)=[CH:80][CH:79]=1

参加物

8

反応物 5

HCID 313Hydrochloric Acid2 回HCID 11776TriphenylphosphineHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamateHCID 537612552-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethanol

生成物 2

HCID 222AmmoniaHCID 57933208(3R)-3-[5-{2-[4-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethanol (Prepared according to WO9843942, 390 mg, 0.88 mmol) was dissolved in tetrahydrofuran (6 ml), triphenylphosphine (344 mg, 1.31 mmol) then di-tert-butyl(E)-diazene-1,2-dicarboxylate (265 mg, 1.31 mmol) was added and the mixture was stirred for 20 minutes. tert-butyl[2-(4-hydroxyphenyl)ethyl]carbamate (Prepared according to WO2004/020415, 311 mg, 1.31 mmol) was then added and the reaction was stirred over night. Hydrogen chloride (4M in diethyl ether, ml) was added and left to stir for 3 days, then hydrochloric acid (2M, 5 ml) was added and after 1 hour the mixture was washed with diethyl ether, basified with 2N sodium hydroxide, extracte with diethyl ether, dried (magnesium sulphate), filtered and the solvents removed in vacuo and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (242/8/0.8 to 95/5/0.5 by volume) to furnish the title compound as a colourless oil, 100 mg.

後処理

  1. stirringthe reaction was stirred over night
  2. waitleft
  3. stirringto stir for 3 days
  4. washwas washed with diethyl ether
  5. dry with materialdried (magnesium sulphate)
  6. filtrationfiltered
  7. customthe solvents removed in vacuo
  8. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane

出典と根拠

ORDレコード
ord-2cc5c67f2d4d40169f0c01cc3b0c53cc
出典データセット
uspto-grants-2009_11
特許番号
US07612084B2

反応ノート

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