tert-Butanol → N-Cbz-4-[(2,3-Dihydroxypropyloxy)phenyl]butylamine

HRID 25119

Reaction equation

HRID 25119 reaction equation
[OH2:1].C[N+]1([O-])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[C:10]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28](OCC=C)=CC=1)([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].OS([O-])=O.[Na+].[C:40]([OH:44])(C)(C)C>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[C:10]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:8][C:7]=1[O:6][CH2:5][CH:4]([OH:1])[CH2:40][OH:44])([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 11551825[4-(4-Allyloxyphenyl)butyl]carbamic acid benzyl esterHCID 23665763Sodium Bisulfite

Product 1

HCID 11559794N-Cbz-4-[(2,3-Dihydroxypropyloxy)phenyl]butylamineYield 62%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 18366337Propan-2-one--water (1/1)Solvent2×

Procedure

A solution of osmium tetroxide (50 mg, 0.2 mmol) in tert-butanol (8 mL) was added to a solution of 4-methylmorpholine N-oxide monohydrate (1.2 g, 9.1 mmol) in 100 mL (1:1) acetone/water solution and the mixture was stirred for 10 min at room temperature. After this time, 30 (3.1 g, 9.0 mmol) was added in 50 mL (1:1) acetone/water solution. The reaction mixture was stirred at room temperature overnight, then NaHSO3 (0.5 g) was added and the stirring was continued for 15 min. The acetone was evaporated and the pH was adjusted to 5.5 by the addition of 2N HCl then the mixture was extracted with ethyl acetate. The organic fraction was isolated, dried with sodium sulfate, and filtered through silica gel. Compound 31 (2.1 g, 62%) was isolated as a white solid after removing the solvent and drying under vacuum. 1H NMR (300 MHz, DMSO-d6) δ 1.48 (m, 2H), 1.50 (m, 2H), 2.46 (m, 2H), 3.00 (m, 2H), 3.43 (m, 2H), 3.80 (m, 2H), 3.93 (t, 1H), 4.66 (d, 1H), 4.99 (s, 2H), 6.82 (d, 2H), 7.07 (d, 2H), 7.26 (s, 1H), 7.33 (s, 5H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. waitthe stirring was continued for 15 min
  3. customThe acetone was evaporated
  4. additionthe pH was adjusted to 5.5 by the addition of 2N HCl
  5. extractionthe mixture was extracted with ethyl acetate
  6. customThe organic fraction was isolated
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered through silica gel

Sources & evidence

ORD record
ord-7aa58a624b334f989ea7484e39e0bc73
Source dataset
uspto-grants-2005_02
Patent number
US06858615B2

Linked notes

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