N-Hydroxyphthalimide → [3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-2,2-dimethyl-propyl]-carbamic acid tert-butyl ester

HRID 494742Notes

Reaction equation

HRID 494742 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[C:13]([O:17][C:18](=[O:26])[NH:19][CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][OH:23])([CH3:16])([CH3:15])[CH3:14].O[N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.ClCCl>[C:13]([O:17][C:18](=[O:26])[NH:19][CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][O:23][N:28]1[C:32](=[O:33])[C:31]2[C:30](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:29]1=[O:38])([CH3:16])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 21263232tert-butyl N-(3-hydroxy-2,2-dimethylpropyl)carbamate

Product 1

HCID 68862491[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-2,2-dimethyl-propyl]-carbamic acid tert-butyl esterYield 11.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethylazodicarboxylate (8.26 mL, 52.4 mmol) was added to a solution of (3-hydroxy-2,2-dimethyl-propyl)-carbamic acid tert-butyl ester (10.2 g, 49.9 mmol), N-hydroxyphthalimide (8.15 g, 49.9 mmol) and triphenylphosphine (13.1 g, 49.9 mmol) in THF (200 mL). The solution was stirred at room temperature for 16 hours after which time it was diluted with dichloromethane and passed through a plug of silica gel, eluting with dichloromethane. The product containing fractions were concentrated to a yellow liquid, which was further purified by flash column chromatography (dichloromethane to 4:1 dichloromethane/ethyl acetate) to provide pure desired product (1.98 g, 11%) as a waxy white solid.

Workup

  1. washeluting with dichloromethane
  2. additionThe product containing fractions
  3. concentrationwere concentrated to a yellow liquid, which
  4. customwas further purified by flash column chromatography (dichloromethane to 4:1 dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-55293c3e53b94aa3aea7887968cd2b1e
Source dataset
uspto-grants-2009_05
Patent number
US07538120B2

Reaction notes

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