tert-Butanol → HCID 19995538, compound

HRID 2249121Notes

Reaction equation

HRID 2249121 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@H:11]([F:19])[C@H:10]1[OH:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(O)(C)(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([F:19])[C:10]1=[O:20])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 159087TriacetoxyperiodinaneHCID 18646607HCID 18646607, compound

Product 1

HCID 19995538HCID 19995538, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-(1S,2S,3R)-3-tert-butoxycarbonylamino-1-fluoro-1,2,3,4-tetrahydro-2-naphthalenol (140 mg) in anhydrous methylene chloride (5 ml) was added Dess-Martin periodinane (340 mg) and tert-butyl-alcohol (70 mg). Stirring was maintained at room temperature for 31/2 hours. The reaction was quenched with isopropanol and the reaction mixture was poured on a silica gel column (50 g, elution with cyclohexane: ethyl acetate, 9:1) to afford the title compound (105 mg) as an oil.

Workup

  1. customThe reaction was quenched with isopropanol
  2. additionthe reaction mixture was poured on a silica gel column (50 g, elution with cyclohexane: ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-fa081b5b26c74290abf064348350fc15
Source dataset
uspto-grants-1991_08
Patent number
US05041673

Reaction notes

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