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

HRID 1766827Notes

Reaction equation

HRID 1766827 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-d72a0673189944ffbceb022c0de16bf4
Source dataset
uspto-grants-2007_06
Patent number
US07230099B2

Reaction notes

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