Lithium Hexamethyldisilazide → HCID 67241769, compound

HRID 335729Notes

Reaction equation

[NH2:1][C:2]1[O:3][CH2:4][C@@:5]2([N:21]=1)[C:18]1[CH:17]=[C:16](Br)[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([OH:20])=[CH:9][CH:10]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(N(C)C)=CC=CC=2)CCCCC1.[CH3:50][C:51]1([CH3:57])[O:56][CH2:55][CH2:54][NH:53][CH2:52]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:1][C:2]1[O:3][CH2:4][C@@:5]2([N:21]=1)[C:18]1[CH:17]=[C:16]([N:53]3[CH2:54][CH2:55][O:56][C:51]([CH3:57])([CH3:50])[CH2:52]3)[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([OH:20])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A 2-5 ml microwave vial was charged with (S)-2-amino-2′-bromo-5H-spiro[oxazole-4,9′-xanthen]-7′-ol (300 mg, 0.864 mmol) (104780-26-0), Pd2dba3 (39.6 mg, 0.043 mmol), 2′-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (40.8 mg, 0.104 mmol) and 2,2-dimethylmorpholine (299 mg, 2.59 mmol). The mixture was capped with argon and LiHMDS (1M in THF) (4321 μL, 4.32 mmol) was added and the vial was sealed and heated at 110° C. in microwave reactor for 1 hr. The reaction mixture was quenched by addition of 2 ml water and EtOAc, then saturated NH4Cl was added. The organic layer was filterd through Celite, concentrated in vacuo and purified on a 40 g RediSep column using 15-80% DCM/MeOH/NH4OH in DCM to afford (R)-2-amino-2′-(2,2-dimethylmorpholino)-5H-spiro[oxazole-4,9′-xanthen]-7′-ol.

Workup

additionwas added
customthe vial was sealed
customThe reaction mixture was quenched by addition of 2 ml water and EtOAc
additionsaturated NH4Cl was added
concentrationconcentrated in vacuo
custompurified on a 40 g RediSep column

Sources & evidence

ORD record: ord-11a4d7484b7c4bde937c366c4fab5959
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883782B2

Reaction notes

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