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Pyrrolidine → Tert-butyl (2S,3R)-3-methoxy-1-oxo-1-(pyrrolidin-1-yl)butan-2-ylcarbamate

HRID 1808778
Notes
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Reaction equation

HRID 1808778 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:13]([O:15][CH3:16])[CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:19]([CH:23]([CH3:25])C)[CH:20]([CH3:22])C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.N1CCCC1>C(Cl)Cl>[CH3:16][O:15][C@H:13]([CH3:14])[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:10](=[O:12])[N:19]1[CH2:20][CH2:22][CH2:25][CH2:23]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 15460346(2S,3R)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxybutanoic acid

Product 1

HCID 86666001Tert-butyl (2S,3R)-3-methoxy-1-oxo-1-(pyrrolidin-1-yl)butan-2-ylcarbamateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(2S,3R)-2-(Tert-butoxycarbonylamino)-3-methoxybutanoic acid (643 mg, 2.76 mmol), which is commercially available, and DIPEA (1.440 mL, 8.27 mmol) was mixed in DCM (10 mL). The mixture was cooled to 0° C. TBTU (974 mg, 3.03 mmol) was added and the mixture stirred at rt for 10 min. Pyrrolidine (0.274 mL, 3.31 mmol) was added and the resultant mixture was stirred at rt for 16 h. The mixture was diluted with DCM (10 mL). The organic phase was washed with NaHCO3 (8% in aq. solution) and brine, filtered through a phase separator and concentrated under reduced pressure. The residue was purified via Biotage (gradient; DCM/iso-propanol, 99:1 to 95:5, KP-SIL 340 g column). The solvent was removed under reduced pressure to give the title compound (0.704 g, 95%). 1H NMR (400 MHz, CD3OD) δ 1.15, 1.44, 1.82-2.05, 3.33, 3.35-3.52, 3.54-3.65, 3.66-3.79, 4.36. Total no of protons: 25. LCMS (M+H)+: 287.

Workup

  1. washThe organic phase was washed with NaHCO3 (8% in aq. solution) and brine
  2. filtrationfiltered through a phase separator
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified via Biotage (gradient; DCM/iso-propanol, 99:1 to 95:5, KP-SIL 340 g column)
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-be2d75e01eab4d32a877bc1d8068468d
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08361998B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes