Naphthalene → 1-(3-(t-butoxy-carbonylamino)-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propyl)cyclohexanol

HRID 1254321Notes

Reaction equation

HRID 1254321 reaction equation
[OH:1][C:2]1([CH2:8][CH:9]([NH:19][CH3:20])[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C1C2C(=CC=CC=2)C=CC=1.C([O-])([O-])=O.[K+].[K+].[C:37]([O:46]N1C(=O)CCC1=O)([O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])=O>C1COCC1.O>[C:14]([O:13][C:12]([NH:11][CH2:10][CH:9]([N:19]([CH3:20])[C:37]([O:39][CH2:40][CH2:41][Si:42]([CH3:43])([CH3:44])[CH3:45])=[O:46])[CH2:8][C:2]1([OH:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)=[O:18])([CH3:16])([CH3:17])[CH3:15]

Participants

6

Reactant 4

HCID 931NaphthaleneHCID 11430Potassium CarbonateHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 59382899Tert-butyl 3-(1-hydroxycyclohexyl)-2-(methylamino)-propylcarbamate

Product 1

HCID 671883231-(3-(t-butoxy-carbonylamino)-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propyl)cyclohexanolYield 86%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of above mixture of tert-butyl 3-(1-hydroxycyclohexyl)-2-(methylamino)-propylcarbamate and naphthalene in 3:1 THF/H2O v/v (4 mL) was added K2CO3 (100 mg, 0.72 mmol), followed by Teoc-OSu (70 mg, 0.27 mmol). The resulting solution was stirred at rt for 30 min and the organic solvent was removed under reduced pressure. The residue was extracted with EtOAc (2×). The combined organic phases were washed with brine, dried, filtered, and concentrated under vacuum. The residue was chromatographed on silica gel to give 1-(3-(t-butoxycarbonylamino)-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)-amino)propyl)cyclohexanol (100 mg, 86% for three steps). MS m/z 453 (M+Na+).

Workup

  1. customthe organic solvent was removed under reduced pressure
  2. extractionThe residue was extracted with EtOAc (2×)
  3. washThe combined organic phases were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-26ea10b2cf354b2b83fdce4e195269f4
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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