(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine → HCID 59211979, compound

HRID 655194Notes

Reaction equation

HRID 655194 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([N:14]2[CH2:19][C:18](=[O:20])[O:17][C:16](=[O:21])[CH2:15]2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O:26][C:27]([NH:29][C@H:30]1[CH2:34][CH2:33][NH:32][CH2:31]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>C1COCC1>[C:22]([O:26][C:27]([NH:29][C@H:30]1[CH2:34][CH2:33][N:32]([C:18](=[O:20])[CH2:19][N:14]([CH2:15][C:16]([OH:17])=[O:21])[C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:9]=2)[CH2:31]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 59212058HCID 59212058, compound

Product 1

HCID 59211979HCID 59211979, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-phenoxyphenyl)morpholine-2,6-dione 26 (4.7 g, 0.0166 mol) in THF (50 mL) was added (3S)-(−)-3-(tert-butoxycarbonylamino)pyrrolidine (4.11 g, 0.0221 mol). The reaction mixture was stirred for 3 days after which time a precipitate had formed. This material was collected by filtration, then washed with ethyl acetate to give the first crop of the title compound. A further crop was obtained by evaporating the filtrate in vacuo. The resultant residue was dissolved in ethyl acetate, washed with 10% hydrochloric acid and brine, dried (Na2SO4) and concentrated in vacuo. The second crop of title compound which precipitated was collected by filtration to give a total yield of 4.36 g (50%), as a cream solid. 1HNMR (300 MHz) (d6-DMSO, 100° C.)) δ 1.43 (9H, s), 1.75-2-20 (2H, 2×m), 2.75-3.1 (1H, br), 3.20-3.75 (4H, m), 4.09 (2H, s), 4.21 (2H, s), 6.22 (1H, br s), 6.37 2H, br t), 6.70 (1H, br), 6.99 (2H, d), 7.14 (2H, m) and 7.37 (2H, br t).

Workup

  1. customhad formed
  2. filtrationThis material was collected by filtration
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-8b49cd907e4b4880b5c9bc4225d54d74
Source dataset
uspto-grants-2011_12
Patent number
US08071582B2

Reaction notes

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