HCID 57432117, compound → HCID 16122905, compound

HRID 2264145Notes

Reaction equation

HRID 2264145 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([C:14]([N:16]([CH2:21][C:22]2[CH:32]=[CH:31][C:25]3[O:26][CH2:27][CH2:28][CH2:29][O:30][C:24]=3[CH:23]=2)[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCO[C@@H](C(N(CC2C=CC3OCCCOC=3C=2)CC(C)C)=O)C1)C1C=CC=CC=1>>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([N:16]([CH2:21][C:22]2[CH:32]=[CH:31][C:25]3[O:26][CH2:27][CH2:28][CH2:29][O:30][C:24]=3[CH:23]=2)[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 57432117HCID 57432117, compoundHCID 57432118HCID 57432118, compound

Product 1

HCID 16122905HCID 16122905, compound

Procedure

(S)-(+)-4-benzyl-N-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylmorpholine-2-carboxamide and (R)-(−)-4-benzyl-N-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylmorpholine-2-carboxamide. Resolution into the pure enantiomers was performed by preparative HPLC using isocratic elution on ChiralPak AD at 1 mL/min, eluting with 100% ethanol. Under these conditions, the (R)-(−)-isomer elutes second after the (S)-(+)-isomer. (S)-(+)-4-benzyl-N-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylmorpholine-2-carboxamide: [α]D25° C.=+10° (c=1, MeOH), (R)-(−)-4-benzyl-N-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylmorpholine-2-carboxamide: [α]D25° C.=−10° (c=1, MeOH)

Workup

  1. washelution on ChiralPak AD at 1 mL/min
  2. washeluting with 100% ethanol
  3. custom[α]D25° C.=+10° (c=1, MeOH), (R)-(−)-4-benzyl-N-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylmorpholine-2-carboxamide
  4. custom[α]D25° C.=−10° (c=1, MeOH)

Sources & evidence

ORD record
ord-f0dcb4d66c454b91bb2e29ca4b05fa58
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Reaction notes

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